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Sissy Stories

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Inadequate, Chapter 6

Our daughter arrives from school unexpectantly and everything changes.

Sunday morning, Cathy went to church as usual. Well, not entirely as usual. She had showered and dressed in her sober Sunday clothes, but Rex teased her pussy mercilessly throughout breakfast so that, when she left for church, her panties were soaked and...

Inadequate, Chapter 1

Feelings of inadequacy lead John down a path of sissification that can only end in degradation and servitude.

Okay, I admit it: I’m a lot happier now. Which just proves that I’m not a real man at all. My name is Gianna and I deserve to be treated like the domestic servant and sex slave I’ve become. I used to be John, husband and father, a respected member of the...

Neighbours - Chapter 71

Crissy has another shift at the toy store

Morning arrived, and I couldn’t quite place the strange sensation I was feeling. It took me a few moments before I identified the sensation as a morning hard-on. The combination of having a plug in me with being uncaged was giving me the freedom to be phy...

"Chrissie" Book II, Chapter 2

Rebecca and her bitchy friends have fun with poor Chrissie -- and impose a major new change

I had taken great pains to symmetrically arrange the cheese wedges, fruit and other nibblers on the serving platter, but Rebecca was too busy ogling a photo on her friend Katie’s cellphone to notice my meticulous craftwork. “Day-um, girl, you hit that?” M...

First Assignment

This is what I sent to Mistress after HER first assignment, with some slight edits to make it fit the format.

Just getting home from the store with a few new items that i purchased specifically so that i could try them on for YOU, i’m nervous and excited as i open the stockings and take the tags off of the panties. This is my first assignment for YOU. Still in my...

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Chrissie Chapter 4

Chrissie makes a deeper committment

My masters had wanted me to get an early start Saturday morning, so by 9:30am I was already in my maid’s uniform scrubbing the hallway baseboards while Rebecca and Karl relaxed in bed smoking a wake-up joint and watching cartoons. From my kneeling positio...

Neighbours - Chapter 56

Thanks to Liam, Crissy and Mallory get closer

I was barely recovering from our shared experience and was now eagerly searching Mallory’s face for clues about his decision. There seemed to be real torment at play. “I… I want to stay. I will just have to make a call…” he finally announced. “Oh, is some...

Becoming Anne - My Feminization Chapter 1

My wife discovers my need to be feminized and begins my makeover to Anne (series)

I walked into our bedroom. Jess, my wife sitting on the bed. Beside her were some of her sexy lacy underthings, items I had been wearing in secrecy. “Please don’t lie to me,” she said. “You have been dressing like a girl, using my clothes, haven’t you?” M...

Adventures in House Sitting — Part 1

A crossdressing sissy takes a two-week house-sitting opportunity to expand her horizons.

It was too good to be true. My daughter, who lived about three hours away, needed someone to house-sit for her for a couple of weeks. I was quasi-retired and able to do what work I did from “home” (read: anywhere I could get an internet connection). My wi...